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Overview

1BR Oceanview Vacation Rental St. John, Virgin Islands USA

Windwardside Guest Cottage is the smallest of the Calabash Cottages group but our guests love it. Our goal in constructing Windwardside Guest Cottage was to provide a romantic haven packed with amenities but at a reasonable price. We have many honeymoon guests that choose Windwardside Guest Cottage for precisely this reason It is a budget home that won’t make you feel like you have made any compromises. But the cottage is not only for honeymoon couples- it is a quaint and lovely cottage for any visitors to the island that want an intimate experience of our beautiful island with a gorgeous view.

IMPORTANT INFO ABOUT RATES AND POLICIES: Our rental week runs from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as listed. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. There are no extra costs for reservations, cleaning or service. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and information about our rentals is easily found..

Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.

We have numerous storage areas in a compact home with a a view that rivals any on the island. At Windwardside Guest Cottage you will wake up in a four poster bed to a gorgeous view of the Caribbean sea framed by palm trees. You could easily create a post card from the view of this adorable cottage.

The interior has a queen-size, four-poster bed, a small seating area, a kitchenette and a breakfast bar. The furnishings are both tasteful and cheerful. The covered porch has a dining area and two lounging chairs where you can enjoy the trade winds or good book while watching the sailboats pass by. A small gas grill is also available if you prefer to prepare your meals over looking the sea. A shower garden opens onto an uncovered deck. There you can have a relaxing evening soak in the hot tub under a starry Caribbean sky. The hot tub also has a wide view of the sea and total privacy.

In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus the dedicated staff of Calabash Cottages who will organize your vacation from start to finish all for the price of a hotel room. We provide snorkel gear, beach chairs and a cooler and a beach umbrella

We also include amenities that you may never need on our casual island (including an iron and a blow dryer) because we want you to be able to travel as light and carefree as possible. Please read reviews from out former guests. We hope to host you on our next visit to St. John.

About Susan Brierley

We are thirty year residents of St. John. My husband is a retired builder and we designed this home together. We built Windwardside in 1996 and have managed it as part of the Calabash Cottages group for over 20 years. Calabash Cottages offers charming and private cottages and villas in quiet secluded locations. Our main focus is to provide an assortment of options for couples in a tranquil setting.

We and our staff always do our best to insure your precious vacation time is well spent at one of our Calabash Cottages. We are very happy to answer any questions to help you decide if Windwardside Guest Cottage or one of our other Calabash Cottages is a good fit for you.

Susan Brierley purchased this cottage in 1996

Why Susan Brierley chose Coral Bay

We love Coral Bay and wanted to design a home that did not tower over the hillside but fit into it's natural surroundings. The shape and orientation allowed of this property allowed us to do just that while still offering fabulous views. We love quiet natural settings, tropical gardens and ocean views and we appeal to visitors who are looking for just that.

What makes this cottage unique

Windwardside Guest Cottage will make you fall in love with the view from the front porch. The first thing you will see in the morning right from your four poster bed is the palm fronds waving in the breeze. This compact cottage offers many amenities. It is also a great choice for two couples when rented with Windwardside Main House as each has a lot of privacy.

(28 traveller reviews)

Caribbean Dream Cottage

For the first time ever, my husband and I decided to vacation in the same place 2 years in a row:Windward Side Cottage in St John. We had such a fairytale perfect time there last year, we knew any other place would probably disappoint in comparison. And Windward Side cottage was every bit as clean, romantic, well-appointed, fun, and comfortable as last year. Susan and her staff think of everything and see to every detail. To wake every morning and see the sunrise and gorgeous view right from your bed, to spend the day face-down in the beautiful calm clear waters of Salt Pond Bay and other great snorkeling beaches around Coral Bay, to spend time chatting with total strangers on this friendly island, to be surprised by baby donkeys and goats around every twisty turn of the road, and to get to love the hair-raising drive up the mountain...all make us miss this beautiful place.

Review Submitted: Apr 15, 2016

Date of Stay: Apr 2016

Source: VRBO, from HomeAway

Owner's Response: Thank you for such a lovely review of Windwardside Guest Cottage and your time on the island. We do our best to anticipate guests needs but it is always nice to hear that we have succeeded. Vacation time is precious I am so happy to hear that you enjoyed yours. Hope to see you again! Susan

Wonderful Vacation!!

Our experience with the Calabash Cottage staff could not have been better, they took care of every detail! We had a wonderful trip and plan to return some day soon. We will most definitely do business with this rental company again. Thanks for everything!

Review Submitted: Feb 29, 2016

Date of Stay: Dec 2015

Source: VRBO, from HomeAway

Owner's Response: Hi Roberta,
We really appreciate your lovely review. I'm so glad that the cottage met your expectations and that you found the staff so helpful. I am very lucky to have them! Hope to see you on another visit. Susan

Great honeymoon stay!

Perfect place for a 2 person getaway! All the staff made planning and everything on travel days go really smooth and stress free--arranging taxis, rental cars, and generally having good advice. The house itself was great, very small but has everything you need. The views from the cottage are amazing. The hot tub was great, we used it every night! The drive up from the main road to the cottage is pretty intimidating, but went well after the first time. Close to quite a few good restaurants on that side of the island. If you cook, make sure to clean the dishes right away and get up any crumbs, as the ants will find their way in quickly (but if you clean well won't be a problem). Also loved the outdoor shower!

Review Submitted: Dec 28, 2015

Date of Stay: Dec 2015

Source: VRBO, from HomeAway

Owner's Response: Thank you so much for taking the time to write a review the day after your departure! I know it must be a busy time do so we really appreciate the effort. You bring up two points that i like to have guests address because they can do so better than we can. Windwardside Guest Cottage was a special place for us to build because we had a particular intent. We wanted to build a small cottage that still had plenty of charm and comfort and we loved the challenge. We wanted visitors to St. John to be able to enjoy a very special place without blowing their budget. We feel a lot of pride in providing a compact space with a charming old time Caribbean feel, a great view. four poster bed and private hot tub. I am also glad that you mentioned the need to discourage insects. In the states it is common to leave sugar bowl on the counter but here.... oh no. Tropical rules apply. If it is open, put it in the fridge is you don't want ants! Even if you do want ant put it in the fridge because the next guests might not:) Thanks for your visit! Susan

Paradise!!!!

The cottage was absolutely a paradise. It was tiny but clean and maintained down to the smallest detail. Breakfasts on the balcony with the stunning view will we never forget.

We have never been so welcomed and taken cared off. The whole arrangement with taxis, pickup and car rental was excellent.

We will be back!!! Thanks for everything!!!

Review Submitted: Jan 18, 2015

Date of Stay: Nov 2014

Source: VRBO, from HomeAway

Owner's Response: Thank you, Therese and Mikael. We are honored to have guests come from so far away to stay at our cottage. I am glad that we were able to live up to your expectations. Thank you for taking the time to review that cottage. I hope that we see you again. Susan

Great surprise birthday gift!

This cottage was all we expected from the exciting pictures on the web. It did not disappoint. The view was even better than expected. Everything was clean and well organized, with many extras helpfully available. The location on the quiet side of the island a dream, with excellent restaurants nearby.

The transportation from the St. Thomas airport to the St. John ferry and back, the car rental, a leisurely stop at the one big supermarket, and the taking us to the cottage upon arrival were all arranged for us as promised. The greeter was terrific! She guided us through all this with patience and many suggestions and information that proved very helpful later.

The car rental agency that was arranged was also helpful, letting us park there when visiting Cruz Bay and even taking us back to the ferry at the end when he saw how much luggage we had.

Four wheel drive is necessary to get to the cottage (Mr. Toad's wild ride up the mountain on dirt roads), but the view and quiet are well worth it (just toads at night, roosters in the morning, and stars overhead.) And four wheel drive (the island is awash in Jeeps) is necessary to get to the great isolated beach at Little Lameshur Bay for swimming and snorkeling.

They promised a 5 star vacation, and it was! Thanks to all.

Review Submitted: Dec 30, 2014

Date of Stay: Dec 2014

Source: VRBO, from HomeAway

Owner's Response: Dear Richard, I am so glad that your birthday surprise for Steve's 60th was a hit. Also, I am happy that you got to explore "little" lameshur. It's one of my favorite snorkel spots that I always take my family to when they visit. Thank you for staying with us and taking the time to write a review.
All the best- Susan

Take me back there, right now.

We had such a glorious time. The cottage is tiny but wonderful -- clean, airy, bright. There's no A/C because it's designed with windows on all sides and a ceiling fan to help the cross-breezes along. We were comfortable in mid-May. It felt like much more of a real island experience than staying in a resort.

I was nervous about privacy because this cottage is attached to a larger house. They told us the plantings would provide privacy, and they really, really do. The entire place is cloaked by beautiful tropical plantings, with the exception of the view straight out to the ocean. The only time you'd see other people is on the path to the shared parking lot, which crosses directly in front of the cottage by the double screen doors right in front of the bedroom. There are curtains you can pull in front of the doors, though.

The garden shower is very private. The wall around it is probably 7 feet tall, with vines and plants coming down the walls. It was awesome.

The views pictured on this website are not exaggerated, btw. I was pretty sure the photos were prettified in some way, but the view is exactly as pictured, and I have a bunch of photos on my camera to prove it. Basically, that's what you see when you're sitting up in bed.

They're not exaggerating about the road, either. The first time we drove up it, we were both white-knuckled. By the end of the week, we were rocking and rolling down that road like old pros. It was great. A little tutorial from the car-rental agency didn't hurt, either.

We used the grill, but we never got around to using the hot tub -- we'd rather have spent our time on the beach. The WiFi was not quite strong enough to stream Netflix, but there is a small TV with a DVD player, so I'd bring DVDs if you want to watch movies at night.

We liked Coral Bay way better than Cruz Bay, the more populous town on the other end of the island. There are far fewer people and more donkeys/chickens in the road, which was amusing, and just as many great beaches. We went over to the west end to visit, but we always ended up preferring Coral Bay.

Word of warning: If you're going to the islands in May or later, be sure to bring plenty of DEET, because the mosquitoes will be out in force, including in the garden shower. As one local told us, "Better spray than dengue."

Review Submitted: Dec 14, 2014

Date of Stay: May 2014

Source: HomeAway

Owner's Response: Thanks for posting about your stay at Windwardside Cottage, Sarah. I'm glad to hear that we lived up your expectations. I especially appreciate your addressing the issue of privacy from the main house. It means much more to potential visitors to hear this from a former guest than directly from us. Sorry- that your trip was during one of the "buggy". It isn't necessarily an issue related to the month of the year. When we get a big rain after a dry period mosquitoes tend to hatch out 5-7 days later. Fortunately, the "bloom" does not usually last very long. Thanks again for staying with us and we hope to see you again. Susan

Location

Nearest Airport

20
Miles

St. Thomas

Nearest Barpub

1
Miles

Shipwreck Landing

Nearest Ferry

8
Miles

Cruz Bay

Nearest Restaurant

1
Miles

Shipwreck Landing

Nearest Beach

2.5
Miles

Salt Pond Bay

Car: necessary

Remote and quiet setting, three quarters of a mile up dirt road with very little traffic. Beautiful view of Coral Bay and nearby islands. Near to beaches, shops restaurants, hiking trails and boating. Shares no facilities with other home on property except parking area.

Additional pricing information

Hotel tax in the Virgin Islands is increasing to 12.5% as of January 1, 2016.
For larger groups the guest cottage can be rented along with the neighboring Windwardside Main House.
For that option, or to see our other cottage for two, Sago Cottage, please see our additional listings on the St. John page.

Check or money order. 50% at time of reservation. Balance due 30 days before arrival.

Manager's Cancellation Policy

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